Реакция #40262

Уравнение реакции

2-chloro-1-methylpyridinium iodide

(1,4-dioxaspiro[4.5]dec-7-en-8-yl) acetic acid

triethylamine

2-iodo-6-methoxyaniline

→

2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-(2′-iodo-6′-methoxy-phenyl)acetamide

Выход 89.6%

2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-(2′-iodo-6′-methoxyphenyl)acetamide

Выход 89.6%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   ТемператураThe reaction mixture is heated
2. 2
   Температураat reflux for 20 hours
3. 3
   ТемператураAfter cooling
4. 4
   Экстракцияacidification with 1N HCl solution to pH=5-6, the mixture is extracted with dichloromethane
5. 5
   ПромывкаThe organic phases are washed with saturated aqueous sodium chloride solution
6. 6
   Сушкаdried over magnesium sulfate
7. 7
   Другоеevaporated under vacuum
8. 8
   ДругоеPurification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 4/6)

Методика

A solution of (1,4-dioxaspiro[4.5]dec-7-en-8-yl) acetic acid (567 mg; 2.86 mmol; 1 eq) (7) and 2-iodo-6-methoxyaniline (1 g; 2.86 mmol; 1 eq) in anhydrous dichloromethane (30 mL) is admixed with 2-chloro-1-methylpyridinium iodide (1.46 g; 5.73 mmol; 2 eq) and triethylamine (3.98 mL; 28.65 mmol; 10 eq). The reaction mixture is heated at reflux for 20 hours. After cooling and acidification with 1N HCl solution to pH=5-6, the mixture is extracted with dichloromethane. The organic phases are washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and evaporated under vacuum. Purification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 4/6) gives 1.10 g of 2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-(2′-iodo-6′-methoxy-phenyl)acetamide (16) in the form of a yellow foam (yield: 90%).

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